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Photochemical release of carbon disulfide from 1,1‐dithiooxalate and the analogous esters (780.10)
Author(s) -
Levy Elizabeth,
DeMartino Anthony,
Bernt Christopher,
Burks Peter,
Pierri Agustin,
Ford Peter
Publication year - 2014
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.28.1_supplement.780.10
Subject(s) - chemistry , carbon disulfide , photochemistry , molecule , alkoxy group , combinatorial chemistry , organic chemistry , alkyl
Carbon disulfide (CS 2 ) is thought to be a biologically relevant molecule that, upon reacting with amines, forms dithiocarbamates, which disrupt nuclear factor κB mediated tumor growth. To insure careful control we have designed a photocatalytic system whereby CS 2 uncaged from the surface of binary chalcogenide cadmium selenide (CdSe) nanocrystalline quantum dots (QD). This is achieved through a hole transfer process to 1,1‐dithiooxalate (DTO) adsorbed to the nanoparticle surface after exciting the QD with visible and near UV light. An analogous photoreaction occurs with the t‐butyl‐ DTO ester. We have also synthesized an octyl‐DTO ester through an acetylation and a subsequent sulfur replacement reaction with chloride substituents. These esters provide a modular system where the photochemical breakdown of the DTO compound could release additional therapeutics. Currently, we are working to synthesize a dye‐functionalized DTO ester to further understand this photochemical process and product distribution. This method may serve as an innovative strategy for the therapeutic release of CS 2 and other potentially useful molecules in various systems.Grant Funding Source : Supported by NSF (CHE‐1058794) and IRES‐ECCI (NSF‐OISE‐1065581)